Flavylium salts as in vitro precursors of potent ligands to brain GABA-A receptors

The synthesis of a series of derivatized flavylium cations was undertaken and the affinity to the benzodiazepine binding site of the GABA-A receptor evaluated. The observed high affinity for some derivatives (sub-mu M range) was explained by an in vitro transformation of the flavylium cations into the corresponding trans-retrochalcones, components which are proposed to be the active species in this series. (C) 2008 Elsevier Ltd. All rights reserved.